Trimethylene glycol disalicylate and method of preparing the same.



ATES PATENT OFFICE;

ALPHONSO M. CLOVER, 015 DETROIT, MICHIGAN, ASSIGNOR. TO PARKE, DAVIS & COM- PANY, OF DETROIT, MICHIGAN, A CORPORATION OF MICHIGAN.

-TRIMETHYLENE GLYCOL DISALICYLATE AND METHOD OF PREPARING THE SAME.

and State of Michigan, have invented certain ene Glycol Disalicylate and Methods of.

sulfuric acid, preferabl in the proportion water which is limited in quantity,

melting-point of about 77 new and usefulI-mprovements in Trimethyl- Preparing the Same, of which the following is a specification.

' The invention consists in a new specific body,

inafter set forth.

The new body lows:

- Trimethylene glycol isfirst treated with may be obtained as folof 100 grams of the trimethylene glycol to grams of concentrated sulfuric acid, the latter being slowly added to the former and the temperature of the mixture being prevented from exceeding 100 C. by surrounding the vessel with water and stirring the mixture as thesulfuric acid is added.

Salicylic acid is then. added, preferably 200 grams, and the resultin mixture heated to'100"v C. in a water-bath, care being taken to prevent access of water-vapor to the mixture by providing a substantially air-tight closure for the vessel.

The reaction product is then poured intfo pre erably to a liter, to facilitate-the recovery of the unchanged salicylic acid. The temperature is brought to about 50 'C. at which temperature the portion which is insoluble in water is liquefied. The solution is then neutralized, preferably by sodium carbonate, and is stirred to extract from the insoluble oily product the unchanged salicylic acid. On cooling, the oily product becomes semisolid and may then be removed by filtration and washed with water. The product is then dissolved in hot alcohol and the trimethylene glycol disalicylate crystallizes out on. cooling. The product may be further purified by recrystallizing from alcohol.

Trimethylene glycol disalicylate has a C. but begins Specification of Letters Patent.

trimethylene glycol disalicylate, and' the'method of preparing the same as hereto about 100 Patented Dec. 10, 1918.

Application filed may 4, 1918. Serial No. 232,488.

to soften 2 or 3 degrees belowthis temperature. The pure substance is colorless, odorless and practically tasteless and insoluble in water. It dissolves readily in benzol, chloroform, acetone and ether and sparinglyin alcohol and petroleum ether. It has valuable medicinal properties, especially in the treatment of rheumatism. It has the empirical formula C H O and its constitution is expressed graphically as follows WhatFI claim as my invention'is: 1. The new body, trimethylene glycol 'disalicylate, having a melting-point of about O l-I 0 and may be expressed graphically asfollows: v

v i -or[ ooocn, A masts, A on 2. The method of producing trimethylene glycol di salicylate, consisting treatlng trimeth lene glycol with sulfuric. acid, addin'g salicylic. acid tothe mixture and heating 0., and cooling and separating the insoluble product by filtration.

3. The methodof producing trimethylene glycol 'disalicylate, consisting in treating trimethylene glycol with sulfuric 'acid at a 'ing the latter by filtration, and purifying by temperature not exceeding 100 C. adding recrystallization. 1

0 salicylic acid and heating to'100 pour- In testimony whereof I afiix my signaing the reaction product into Water and ture in presence of two Witnesses.

5 bringing to about 50 0., the temperature ALPHONSO M. CLOVER.

being sufliciently high so that the portion Witnesses: insolublein Water is liquefied, neutralizing, CHARLES M. WINBRUFF,

cooling to solidify the oily product, separat- GEORGE J. HAINES. 

